Azole derivatives of naphthalenone oxime esters

ABSTRACT

The invention relates to compounds useful as fungicides and plant growth regulants represented by the formula ##STR1## in which: R is a substituent or a group of substituents representing halogen, lower alkyl of 1 to 6 carbon atoms, phenyl, substituted phenyl, phenoxy, substituted phenoxy, naphthyl, nitro, cyano, lower alkoxy, alkoxycarbonyl, or trifluoromethyl; 
     X is single bond, oxygen, sulfur or sulfonyl; 
     G is CH or nitrogen atom; 
     m is an integer from 1 to 4 and a process of making the compound.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention is directed to a new class of oxime derivatives ofα-azolyl naphthalenones. More specifically, the present invention isdirected to a new class of oxime derivatives of α-azolyl naphthalenonesuseful as fungicides and plant growth regulants.

2. Background of the Prior Art

The control of phytopathogenic fungi is of great economic importancesince fungal growth on plants or on parts of plants, i.e., fruits,blossoms, foliage, stems, tubers, roots, inhibits production of foliage,fruit or seed and the overall quality of the harvested crop.

Obviously, fungicides are well known in the art. However, the continuouseconomic toll, discussed above, taken by fungi establish a continuingneed to develop new, more effective fungicides which possess curative,preventative and systemic action to protect cultivated plants. Thoserequirements must be accomplished without any adverse side effects,caused by the fungicide, on the plants to be protected.

Another need in the art is the continual requirement to develop new andeffective plant growth regulants. As in the case of fungicides, there isa continuing need in the art to develop new and better plant growthregulants which regulate the growth of plants. It will be understoodthat the term plant as used herein includes plant parts such as foliage,roots, flowers, stems and seeds. Depending on crop, variety, dosage,time of application and certain cultural practices, growth regulatingeffects which may be obtained include one or more of the following:dwarfing, cessation of terminal growth, inhibition or stimulation ofaxillary and intercalary growth, retardation or stimulation of internodeelongation, inhibition or stimulation of flowering or reproductivedevelopment, and the like. Especially desirable are plant growthregulants that retard or inhibit undesirable growth, such as excessfoliage, stems, branches, etc., of important crops without adverselyaffecting the yield and quality of the commercial crop to be harvested.

U.S. Pat. No. 4,309,434 describesa-phenyl-1-oximins-2-(1,2,4-triazol-1-yl)-ethanes which possessfungicidal properties. The oximins-triazolyl-ethanes of '434 arestructurally distinguished from the oxime derivatives of α-azolylnaphthalenones.

U.S. Pat. No. 4,377,697 is directed to a class of imidazole hydrazoneand hydrazine derivatives. These compounds are also structurallydistinguished from the instant invention. The compounds of thisdisclosure are described as possessing anti-anaerobe and anti-fungalactivity.

Azolylacetophenone oxime ether compounds are disclosed in both Ger.Offen. DE No. 3,244,985 EP No. 113,839 and Ger. Offen. DE No. 3,343,415EP No. 146,047. These compounds are recited to possess fungicidalactivity and plant growth regulation. These compounds differstructurally from the oxime derivatives of α-azolyl naphthalenones inthat the triazolyl group is not attached to a cyclic ring as is the caseof the instant invention.

The above remarks establish the need in the art for new and improvedfungicides and plant-growth regulants. The above discussion,furthermore, emphasizes the uniqueness of oxime derivatives ofnaphthalenone compounds. Such compounds are not only not disclosed inthe art, but no teaching of their use as fungicides or plant-growthregulants is made.

BRIEF DESCRIPTION OF INVENTION

This invention relates to novel oxime derivatives of α-azolylnaphthalenones useful as fungicides and plant growth regulants and canbe represented by formula (I). ##STR2## in which:

R is a substituent or a group of substituents representing halogen,lower alkyl of 1 to 6 carbon atoms, phenyl, optionally substitutedphenyl, phenoxy, optionally substituted phenoxy, naphthyl, nitro, cyano,low or alkoxy, alkoxycarbonyl, or trifluoromethyl;

X is single bond, oxygen, sulfur or sulfonyl;

G is CH or nitrogen atom;

m is an integer from 1 to 4.

Compounds of formula (I) are prepared by reacting an oxime azole (II)with a halide (III) in an inert hydrocarbon solvent such as toluene,xylene, benzene or chlorobenzene with vigorous stirring in the presenceof a phase transfer catalyst and either a powdered metalhydroxide--preferably sodium hydroxide or potassium hydroxide--or aconcentrated aqueous solution of the same. The reaction is carried outat a temperature ranging from ambient temperature to refluxingtemperature of the solvent. In the cases of bromide (III,Y=Br), theambient temperature is preferred. In the cases of a less reactivechloride (III,Y=Cl), the refluxing temperature is preferred.

Suitable phase transfer catalysts are for example trialkylbenzylammoniumor tetraalkylammonium halides preferably with 4 to 12 carbon atoms inthe alkyl radical.

In carrying out the process according to the invention, 1 to 1.5equivalent of halide (III) is preferably employed per mole of the oximeazole of formula (II). In order to isolate the product of formula (I),the reaction mixture is freed from the reaction medium, and water and anorganic solvent are added to the residue. The organic phase is separatedoff and worked up in the conventional manner. ##STR3##

Az=1,2,4-triazole, imidazole

Y=Cl, Br

X, R and m as previously defined.

Compounds of structure (I) form salts with organic and inorganic acids.These salts can be obtained in a simple manner by common salt formationmethods, for example by dissolving a compound of formula (I) in asuitable inert solvent and adding the acid. Diethylether and toluene aretwo common solvents. The resulting salts can be isolated in anyconventional manner, such as by filtration and, if appropriate,purifying by washing with an inert organic solvent. The physiologicallyacceptable salts are also intended to be within the scope of thisinvention.

It should be noted that compounds of structure (I) may exist as syn andanti isomeric mixture. Such isomers are not necessarily separated andtheir mixture are also intended to be within the scope of thisinvention. ##STR4##

The oxime azoles of formula (II) are novel and can be prepared byreacting an azole ketone (IV) with hydroxylamine in an alcoholicsolvent, preferably ethanol, at temperatures between 20° C. and 80° C.,preferably at reflux temperature. The hydroxyalamine is preferablyemployed in the form of its hydrochloride salt (V) in the presence of anacid-binding agent such as pyridine. ##STR5##

a. Az=imidazole

b. Az=1,2,4-triazole Imidazole ketone (IV a) is known (Chemical AbstractRegistry No. [84391-39-9] whereas triazole (IV b) is novel and may beprepared by reaction of the bromoketone (VI) (Chemical Abstract RegistryNo. [13672-07-6] with 1,2,4-triazole by methods disclosed by P. A. J.Janssen et al, in J. Med. Chem. 1969, 12, 784, whose disclosure isincorporated herein by reference. ##STR6## Organic halides of formula(III) are generally known in the literature and can be prepared by thoseskilled in the art.

More preferably, the compounds in this invention have structuresrepresented by formula (I). ##STR7## where

R is a substituent or a group of substituents representing halogen,nitro, cyano, lower alkoxy or trifluoromethyl;

X is single bond

G is CH or nitrogen atom

m is an interger from 1 to 4

The compounds having the structural formula (I) are useful in a processfor controlling phytopathogenic fungi. In this process a fungicidallyeffective amount of the compound having a structural formula (I) inwhich:

R is a substituent or a group of substituents representing hydrogen,halogen, lower alkyl of 1 to 6 carbon atoms, phenyl, optionallysubstituted phenyl, phenoxy, optionally substituted phenoxy, naphthyl,nitro, cyano, lower alkoxy, alkoxycarbonyl, or trifluromethyl;

X is single bond, oxygen, sulfur or sulfonyl;

G is CH or nitrogen atom;

m is an integer from 1 to 4 is applied to the locus under attack by saidfungi.

More preferably, the process for controlling fungi comprises applying afungicidally effective amount of the compound having the structuralformula (I) where

R is a substituent or a group of substituents representing halogen,nitro, cyano, lower alkoxy or trifluoromethyl;

X is a single bond

G is CH or nitrogen atom

m is an integer from 1 to 4 to the locus under attack by said fungi.

In a first preferred embodiment, the method by which a fungicidallyeffective amount of the compound having structural formula (I) isapplied to the plants to be protected from phytopathogenic fungi is byapplication of the compound having the structural formula (I) to thefoliage of the plants to be protected. This compound is applied to thefoliage in a concentration of 0.125 to 10 kilograms per hectare (kg/ha).More preferably, the embodiment wherein fungi are controlled in aprocess comprising applying a fungicidally effective amount of thecompound having structural formula (I) entails applying 0.125 to 5.0kg/ha of compound (I) to the foliage of the plants to be protected fromsaid phytopathogenic fungi.

In the second preferred embodiment of the process for controllingphytopathogenic fungi, a fungicidally effect amount of the compoundhaving the structural formula (I) is applied to the soil in which theplants to be protected from phytopathogenic fungi are grown. In thisembodiment, the compound having the structural formula (I) is applied tothe soil in which the plants to be protected are grown at aconcentration of 10 to 500 mg/l. The exact dosage, within thisconcentration range, is dictated by the fungi to be controlled and theparticular plants to be protected.

As those skilled in the art are aware, the first preferred embodiment ofthe process for controlling fungi is the foliage method. The secondpreferred embodiment is the systemic method of application. Eithermethod may be utilized prior to infection or after fungi attack hasbegun.

Alternately, in yet another embodiment of the process of the presentinvention for controlling phytopathogenic fungi, the compound having thestructural formula (I) may be applied to the seeds as a coating. Thismethod provides plant protection from dangerous fungi by eitherchemotherapeutic means or systemic means or both. That is, the coatingto the seed may protect the soil from infection by the fungi or may betaken up by the plant systemically to protect the plant from the fungalattack. In this seed coating method, the appropriate concentration ofthe compound having the structural formula (I) is in the range ofbetween 5 and 75 grams of compound per 100 kg. of seed.

In still another aspect of the present invention, a process forregulating growth of a plant is provided. In this process a plant growthregulant effective amount of the compound having structural formula (I),where R, X, G and m have the meanings given for compound (I), is appliedto the plant whose growth is to be regulated.

As a plant growth regulant, the preferred compounds are those where R ishydrogen or a halogen, X is a single bond or oxygen, G is nitrogen or CHand m is 1 to 4. More preferable compounds are those in which R is H, Clor Br, X is a single bond, G is nitrogen, and m is 1 or 2.

Yet another important aspect of the present invention involves thedisclosure of new fungicidal compositions. The fungicidal composition ofthe present invention comprises a fungicidally effective amount of thecompound having the structural formula (I), where R, X, G and m have themeanings given for compouad (I), and a carrier therefor.

More preferably, the fungicidal composition comprises a fungicidallyeffective amount of the compound having structural formula (I), whereinthe meanings of R, X, G and m have the preferred meanings for thecompound having structural formula (I), and a carrier therefor.

In a final aspect of the present application a plant growth regulantcomposition is provided. This composition comprises a plant growthregulant effective amount of the compound having the structural formula(I), where R, X, G and m have the meanings given for compound (I), and acarrier therefor.

More preferably, a plant growth regulant composition is disclosed whichcomprises a plant growth regulant effective amount of the compoundhaving structural formula (I) wherein the preferred meanings of R, X, Gand m are those given for the preferred embodiment of the compoundhaving structural formula (I), and a carrier therefor.

The carrier employed in the fungicidal and plant growth regulantcompositions may be a finely divided or granular organic or inorganicinert material. Among the inert carriers within the contemplation ofthis invention are attapulgate clay, sand, vermiculite, corncobs,activated carbon and mineral silicates such as mica, talc, pyrophylliteand clays.

In another preferred embodiment of carrier employed in the compositionof this invention, the carrier comprises a solution. That is, the activeagent, a compound whose structural formula is (I) is dissolved in asuitable solvent which acts as the carrier. Among the solvents, actingas carrier, within the contemplation of this invention are acetone,methanol, isopropanol, t-butyl alcohol, cyclohexanol, n-butyl alcohol,cyclohexanone, toluene, xylene, dioxane, dimethylformamide,dimethylsulfoxide, ethylene dichloride, diacetone alcohol, andN-methylpyrrolidone.

In still another preferred embodiment of the carrier utilized in thecomposition of the present invention, the carrier comprises a wateremulsion. The water emulsion is prepared from a solution as describedimmediately above. To the solution is added a surface active agent.Surface active agents suitable for use in forming the emulsion of thisinvention are known to those skilled in the art. McCutcheon's Detergentsand Emulsifiers, Allured Publishing Corp., Ridgewood, New Jersey (1970);U.S. Pat. Nos. 2,514,916, Columns 2 to 4; and 2,547,734, Columns 3 and4, provide detailed examples of such surface active agents. The surfaceactive agents may be anionic, non-ionic or cationic.

In still another embodiment of a carrier used in the composition of thepresent invention, the carrier is a dispersant. In this embodiment, theactive agent, the compound having structural formula (I), is mixed witha dispersant. The dispersant includes a solvent of the type describedabove, one of the above-described surface active agents and water. Theactive agent is dissolved in the solvent to form a solution. The solventis dispersed in the water with the aid of the surface active agent.

In still another embodiment of the carrier constituent of thecomposition of the present invention, the active compound, the compoundhaving the structural formula (I), is premixed with an inert solidcarrier which is added to a surface active agent and water to provideanother form of dispersion type carrier within the contemplation of thecomposition of this invention.

The embodiment discussed immediately above, the disposal of the compoundhaving the structural formula (I) on a solid inert carrier which isdispersed in the liquid to form a dispersion, may alternatively beemployed in a non-liquid form. That is, the composition of thisinvention may take the form of dust, granules or a paste of a wettablepowder. In these embodiments the active compound of this invention, thecompound having the structural formula (I), is admixed with an inertsolid carrier to form a solid composition. Thus, for example, in theembodiment wherein a powder is formed, the solid inert carrier isprovided in powder form. In many such cases the inert carrier is amineral silicate. The solid may be made wettable by the addition of asurface active agent, well known to those skilled in the art, andreferred to in the above-recited references directed to surface activeagents.

In a final embodiment of the carrier component of the composition ofthis invention, the carrier is an aerosol. To prepare an aerosol, theactive compound is dissolved in a first solvent. This first solvent isconventional in the sense that although it is volatile it is not highlyvolatile. This solution is then admixed with a highly volatile solvent,a so-called liquid aerosol carrier. The aerosol carrier is liquid onlyunder elevated pressure. At ordinary temperatures and at atmosphericpressure, the aerosol carrier is a gas. In a subembodiment of thispreferred carrier, the aerosol carrier may itself be active. Forexample, the carrier may be an insecticide, a herbicide, a bactericideor the like.

Among the carriers discussed above, the carriers comprising solvents andemulsions are particularly preferred in the production of the fungicidaland plant growth regulant compositions of the present invention.

The following examples are given to illustrate the scope of the presentinvention. Because these examples are given for illustrative purposesonly, the invention embodied herein should not be limited to the actualexamples provided.

EXAMPLE 1 Preparation of3,4-Dihydro-2-[1H-1,2,4-triazol)-1-yl)]-1(2H)-naphthalenone

To a mixture of 15 g 1,2,4-triazole, 30 g potassium carbonate and 250 mlacetonitrile at 45° C. was added a solution of 45 g2-bromo-3,4-dihydro-1(2H)-naphtalenone in 150 ml acetonitrile over 2hours. The mixture was kept at 45° C. for 5 hours, then brought togentle reflux for 4 hours. The solid was filtered off, the filtrateevaporated to dryness and the residue taken up in methylene chloride.This was then washed with water, dried over sodium sulfate andevaporated to give a light brown solid. Recrystallization from tolueneyielded 42 g of the titled compound, m.p.=96°-98° C.

EXAMPLE 2 Preparation of 3,4-Dihydro-2-[1H-(1,2,4-triazol)-1-yl]-1(2H)-naphthalenone; Oxime

A mixture of 16.3 g3,4-dihydro-2-[1H-(1,2,4-triazol)-1-yl]-1(2H)-naphthalenone, 5.8 ghydroxylamine hydrochloride, 6.7 g pyridine and 100 ml absolute ethanolwas refluxed for 2 hours, then cooled and poured slowly into 300 ml ofice-cold water. The resulting precipitae was collected, filtered andwashed with n-hexane to give 13.5 g of the titled oxime, m.p.=185°-186°C.

EXAMPLE 3 Preparation of3,4-Dihydro-2-[1H-(1,2,4-triazole)-1-yl]-1(2H)-naphthalenone,O-[(2-bromophenyl)methyl]oxime(Compound No. 37)

To a mixture of 1.45 g3,4-dihydro-2-[1H,2,4-triazol)-1-yl]-1(2H)-naphthalenone oxime, 1 gtriethylbenzylammonium bromide, 100 ml of 25% aqueous sodium hydroxideand 100 ml toluene at room temperature was added, over 20 minutes, 1.6 gof 2-bromobenzyl bromide. The mixture was stirred for 16 hours, thenfiltered and the organic phase separated. The aqueous phase wasextracted with toluene and the combined organic phase washed with waterand dried over sodium sulfate. Upon work-up 2.5 g of the titled compoundwas obtained as a yellow oil. NMR (CDCl₃)δ: 6.9-8.2(10H,m), 6.0(1H,t),5.26(2H,S), 1.8-2.9(4H,m).

EXAMPLE 4 Preparation of3,4-Dihydro-2-[(1H-imidazol)-1-yl]-1(2H)-napthalenone-,O-[(4-fluorophenyl)methyl]oxime (Compound No. 22)

In a manner analogous to the preparation of Example 3, 2.9 g of3,4-dihydro-2-[(1H-imidazol)-1-yl[-1(2H)-napthalenone oxime was reactedwith 2.5 g of 4-fluorobenzyl bromide in the presence of 1 gtetrapentylammonium iodide to give 4.8 g of the titled oxime ether as anoil. NMR (CDCl₃)δ:8.1(1H,m), 6.7-7.5(10H,m), 5.75(1H,t), 5.1(2H,S),2.5-2.8(2H,m), 1.9-2.3(2H,m).

EXAMPLE 5 Preparation of3,4-Dihydro-2-[1H-imidazol)-1-yl]-1(2H)-naphthalenone-, O-[4-(trifluoromethyl)phenyl]methyl oxime (Compound No. 47)

A mixture of 3 g 3,4-dihydro-2-[(1H-imidazol)-1-yl]-naphthalenone oxime,2.6 g 4-(trifluoromethyl)benzyl chloride, 1 g tetrabutylammonium iodide,100 ml of 25% aqueous sodium hydroxide and 100 ml toluene was refluxedfor 7 hours. The reaction mixture was worked up as previously describedto give 3.9 g of the titled oxime ether. NMR (CDCl₃)δ:8.05(1H,m),6.8-7.7(10H,m), 5.8(1H,t), 5.2(2H,S), 2.5-2.8(2H,m), 2.0-2.5(2H,m).

EXAMPLE 6 Preparation of3,4-Dihydro-2-[(1H-1,2,4-triazol)-1-yl]-1-(2H)-naphthalenone-,O-[-4-(chlorophenoxy)butyl]oxime(Compound No. 21)

To a mixture of 3 g3,4-dihydro-2-[1H,1,2,4-triazol)-1-yl]-1(2H)-naphthalenone oxime, 1.2 gpowdered potassium hydroxide and 0.9 g benzyltriethylammonium bromide in30 ml toluene was added 3.6 g of 4-(chlorophenoxy)-1-bromobutane. Thereaction mixture was stirred at 80°-100° C. for 2 hours. The toluenelayer was washed with water; then dried (sodium sulfate) and worked upto give 5.3 g of a light brown oil. NMR (CDCl₃)δ:7.8-8.2(3H,m),6.7-7.4(7H,m), 5.9(1H,t), 4.2(2H, broad t), 3.8(2H, broad t),2.5-2.9(2H,m), 2.25-2.5(2H,m), 1.4-2.1(4H,m).

EXAMPLE 7 Preparation of3,4-Dihydro-2-[2H-imidazol)-1-yl]-1(2H)-naphthalenone-,O-[3-phenoxyphenyl)methyl]oxime(Compound No. 66)

In a manner analogous to the preparation of Example 5, 3 g of3,4-dihydro-2-[(1H,imidazol)-1-yl]-1(2H)-naphthalenone oxime was recatedwith 2.g of 3-phenoxybenzyl chloride in the presence of 1 gtetrabutylammonium iodide to give 4 g of the tilted oxime ether. NMR(CDCl₃)δ:8.05 (1H,m), 6.7-7.5(15H,m), 5.8(1H,t), 5.1 (2H,S), 2.55-2.8(2H,m), 1.9-2.4(2H,m).

EXAMPLE 8 Preparation of3,4-Dihydro-2-[(1H-1,2,4-triazol)-1-yl]-1-(2H)-naphthalenone-,O-[3-[[4-1,1-dimethylethyl)-2-methylphenyl]thio]propyl]oxime(Compound No. 45)

In a manner analogous to the preparaton of Example 3, 3 g of3,4-dihydro-2-[(1H-12,4-triazol)-1-yl]-3-[[4-tertbutyl)-2-methylphenyl]thio]propylbromide in the presence of 1 g tetrabutylammonium iodide to give 5 g ofthe titled oxime ether as an oil. NMR ((CDCl₃)δ:7.9-8.2(2H,m),7.0-7.4(7H,m), 5.9(1H, broad t), 4.25(2H,t), 2.65-3.1(4H,m), 2.4(3H,S),1.8-2.2(4H,m), 1.3(9H,S).

EXAMPLE 9 Preparation of3,4-Dihydro-2-[1H-imidazol)-1-yl]-1(2H)-naphthalenone-,O-[(4-fluorophenyl)methyl]oxime,hydrochloride (Compound No. 33)

A solution of 1 g 3,4-dihydro-2-[(1H-imidazol)-1-yl](2H)-naphthalenone,O-[(4-fluorophenyl)methyl]oxime in 100 ml of diethyl ethyl was treatedwith a steady stream of hydrogen chloride gas until precipitation ofsalt ceased. The precipitate was collected by filtration and air-driedto yield 1 g of white solid, m.p.=171°-174° C.

EXAMPLE 10 Preparation of3,4-dihydro-2-[1H-1,2,4-triazol)-1-yl]1(2H)-naphthalenone-,O-[2-fluorophenyl)methyl]oxime,sulfate(Compound No. 39)

A solution of 1.3 g concentrated sulfuric acid was added dropwise to asolution of 4.4 g3,4-dihydro-2-[1H-1,2,3-triazol)-1-yl]-,O-[(2-chlorophenyl)methyl]oximein 100 ml of toluene at 0° C. The solid settlement was collected bydecantation, then triturated with methylene chloride-diethyl ether mixedsolvent. Trituration was repeated once more with fresh solvent. Theresulting solid was collected by filtration and air-dried to give 3.5 gof the titled sulfate, m.p.=104°-110° C.

EXAMPLE 11 Preparation of Compound Nos. 1-20, 23-32, 34-36, 38, 40-44,46, 48-65 and 67-81

Compound Nos. 1-20, 23-32, 34-36, 38, 40-44, 46, 48-65 and 67-73 wereprepared in accordance with the procedures enumerated in Example 1-10.These compounds are tabulated in Table I. Table I defines the compoundsand characterizes them either by their melting point or by nuclearmagnetic resonance (NMR) data. Compounds 37, 22, 47, 21, 66, 45, 33 and39 prepared in accordance with the procedures of Example 1-10,respectively, are included in the table for completeness. The followingabbreviations and symbols are used to express the NMR data in Table I:s=singlet; t=triplet; q=quartet; d=doublet: m=multiplet σ=ppm relativeto TMS and H=proton.

                                      TABLE I                                     __________________________________________________________________________    Cpd                                Melting Point (°C.) or NMR                                             (delta,                                    No.                                                                              R             X   m G           CDCl.sub.3                                 __________________________________________________________________________    1  H             0   2 N           8.5 (1H,s), 7.9 (1H,s),                                                       7.75-8.1 (1H,m), 6.7-7.5 (8H,m), 6.05                                         (1H,t), 4.0-4.5 (broad t + t), 2.7                                            (2H,m), 2.2 (2H,m).                        2  H             0   3 N           8.1 (1H,m), 7.95 (1H,s),                                                      7.9 (1H,s), 6.75-7.45 (8H,m), 5.9                                             (1H,t), 4.35 (2H,t), 3.9 (3H,t) 2.7                                           (2H,m), 2.4 (2H,m), 2.1 (2H,m).            3  H             0   4 N           8.15 (1H,m), 8.0 (1H,s),                                                      7.95 (1H,s), 6.75-7.5 (8H,m),                                                 5.95 (1H,t), 4.3 (2H,m),                                                      3.9 (2H,m), 2.7 (2H,m),                                                       2.1-2.6 (2H,m), 1.55-2.0 (4H,m).           4  H             Single                                                                            1 CH          MP = 105-108° C.                                     Bond  (HNO.sub.3)                                            5  H             Single                                                                            1 CH          8.1 (1H,m), 7.0-7.5                                         Bond              10H,m), 6.8 (1H, broad s),                                                    5.8 (1H,t), 5.15 (2H,s),                                                      2.7 (2H,m), 2.2 (2H,m).                    6  H             Single                                                                            1 N           8.1 (1H,m), 7.9 (1H,s),                                     bond              7.85 (1H,s), 6.9-7.4 (8H,m),                                                  5.9 (1H, broad t) 5.1 (2H,s),                                                 2.5 (2H,M), 2.3(2H,m).                     7  2-Cl          Single                                                                            1 N           8.1 (1h,m), 7.9 (1H,s),                                     bond              7.85 (1H,s), 6.9-7.4 (7H,m),                                                  6.0 (1H, broad t), 5.2 (2H,s),                                                2.65 (2H,m), 2.3 (2H,m).                   8  3-Cl          Single                                                                            1 N           8.0 (2H,m), 7.9 (1H,s),                                     bond              6.9-7.4 (7H,m), 5.95 (1H, broad t),                                           5.1 (2H,s), 2.6 (2H,m), 2.3 (2H,m).        9  4-Cl          Single                                                                            1 CH          8.0 (1H,m), 6.95-7.5 (9H,m),                                bond              6.75 (1H,s), 5.75 (1H,t), 5.1 (2H,s),                                         2.6 (2H,m), 2.2 (2H,m).                    10 3-Cl          Single                                                                            1 CH          8.0 (1H,m), 6.9-7.5 (9H,m),                                 bond              6.8 (1H,s), 5.8 (1H,t), 5.1 (2H,s),                                           2.65 (2H,m), 2.2 (2H,m).                   11 2-Cl          Single                                                                            1 CH          8.05 (1H,m), 7.0- 7.5 (9H,m),                               bond              6.8 (1H,s), 5.85 (1H,t), 5.25 (2H,s),                                         2.65 (2H,m), 2.15 (2H,m).                  12 H             0   2 CH          8.05 (1H,m), 6.8-7.5 (H,m),                                                   6.75 (1H,s), 5.7 (1H,t), 4.4 (2H,m),                                          4.1 (2H,m), 2.65 (2H,m), 2.15 (2H,m).      13 H             0   3 CH          8.0 (1H,m),                                                                   6.75-7.5 (11H,m), 5.7 (1H,t),                                                 4.3 (2H,t), 3.8 (2H,t) 2.6 (2H,m),                                            1.8-2.4 (4H,m).                            14 H             0   4 CH          8.0 (1H,m), 6.7-7.4 (11H,m),                                                  5.7 (1H, broad t), 4.2 (2H,m),                                                3.8 (2H,m), 2.6 (2H,m), 2.1 (2H,m),                                           1.5-2.0 (4H,m).                            15 4-Cl          0   2 CH          8.1 (1H,m), 6.7-7.5 (10H,m),                                                  5.75 (1H,t), 4.4 (2H, broad t),                                               4.15 (2H, broad t), 2.75 (2H,m),                                              2.25 (2H,m).                               16 4-Cl          0   3 CH          8.1(1H,m),                                                                    6.65-7.5 (10H,m), 5.75 (1H,t),                                                4.3 (2H,t), 3.7 (2H,t), 2.7 (2H,m),                                           1.7-2.4 (4H,m).                            17 4-Cl          0   4 CH          8.1 (1H,m),                                                                   6.65-7.4 (10H,m), 5.75 (1H,t),                                                4.2 (2H, broad t), 3.8 (2H, broad t),                                         2.65 (2H,m), 2.2 (1H,m),                                                      1.4-1.9 (4H,m).                            18 4-Cl          0   1 N           7.8-8.2 (2H,m), 7.9 (1H,s),                                                   6.9-7.5 (7H,m), 5.9 (1H, broad t),                                            5.1 (2H,s), 2.65 (2H,m),                                                      1.8-2.45 (2H,m).                           19 4-Cl          0   2 N           8.0 (1H,m), 7.95 (1H,s),                                                      7.85 (1H,s), 6.7-7.4 (7H,m),                                                  5.9 (1H, broad t), 2.45 (2H,t),                                               4.15 (2H,t), 2.7 (2H,m),                                                      1.8-2.45 (2H,m).                           20 4-Cl          0   3 N           8.0 (1H,m), 7.95 (1H,s),                                                      7.85 (1H,s), 6.65-7.4 (7H,m),                                                 5.9 (1H,t), 4.3 (2H,t), 3.75 (2H,t),                                          2.65 (2H,m), 2.3 (2H,m), 2.0 (2H,m).       21 4-Cl          0   4 N           7.8-8.2 (3H,m),                                                               6.7-7.4 (7H),m), 5.9 (1H,t),                                                  4.2 (2H, broad t), 3.8 (2H, broad t),                                         2.5-2.9 (2H,m), 2.25-2.5 (2H,m),                                              1.4-2.1 (4H,m).                            22 4-F           Single                                                                            1 CH          8.1 (1H,m), 6.7-7.5 (10H,m),                                bond              5.75(1H,t), 5.1 (2H,S), 2.5-2.8                                               (2H,m),                                                                       1.9-2.3 (2H,m).                            23 4-F           Single                                                                            1 N           8.1 (1H,m), 7.9 (1H,s),                                     bond              7.85 (1H,s), 6.8-7.5 (7H,m),                                                  5.95 (1H,t), 5.1 (2H,s), 2.7 (2H,m),                                          1.9-2.5(2H,m).                             24 2-F           Single                                                                            1 CH          8.1 (1H,m), 6.8-7.5 (10H,m),                                bond              5.9 (1H,t), 5.3 (2H,s), 2.75 (2H,m),                                          2.25 (2H,m).                               25 2-F           Single                                                                            1 N           8.05 (1H,m), 7.85 (2H,s + s),                               bond              6.8-7.5 (7H,m), 5.95 (1H,t),                                                  5.2 (2H,s), 7.7 (2H,m), 2.7 (2H,m),                                           1.9 (2H,m).                                26 3-F           Single                                                                            1 CH          8.1 (1H,m), 6.8-7.5 (10H,m),                                bond              5.9 (1H,t), 5.2 (2H,s), 2.8 (2H,m),                                           2.3 (2H,m).                                27 3-F           Single                                                                            1 N           8.05 (1H,m), 7.92 (1H,s),                                   bond              7.9 (1H,s), 6.8-7.5 (7H,m),                                                   6.0 (1H,t), 5.15 (2H,s),                                                      2.75 (2H,m), 1.9-2.6 (2H,m).               28 4-Br          Single                                                                            1 CH          8.0 (1H,m),                                                 bond              6.75-7.5 (10H,m), 5.8 (1H,t),                                                 5.1 (2H,s), 2.7 (2H,m), 2.2 (2H,m).        29 4-Br          Single                                                                            1 N           8.05 (1H,m), 7.94 (1H,s),                                   bond              7.9 (1H,s), 7.0-7.5 (7H,m),                                                   5.98 (1H,t), 5.1 (2H,s), 2.75 (2H,m),                                         2.0-2.6 (2H,m).                            30 4-Br          Single                                                                            1 CH          8.0 (1H,m), 6.9-7.5 (9H,m),                                 bond              6.8 (2H,s), 5.8 (1H,t), 5.1 (2H,s),                                           2.7 (2H,m), 2.2 (2H,m).                    31 3-Br          Single                                                                            1 N           8.0 (1H,m), 7.9 (2H,s + s),                                 bond              6.9-7.5 (7H,m), 5.95 (1H, broad t),                                           5.05 (2H,s), 2.7 (2H,m), 1.8-2.5                                              (2H,m).                                    32 4-Br          Single                                                                            1 N           MP = 164-167° C.                                     bond  (HCl)                                                  33 4-F           Single                                                                            1 H           MP = 171-174° C.                                     bond  (HCl)                                                  34 4-F           Single                                                                            1 N           MP = 159-162°  C.                                    bond  (HCl)                                                  35 4-Br          Single                                                                            1 CH          MP = 162-165° C.                                     bond  (HCl)                                                  36 2-Br          Single                                                                            1 CH          8.05 (1H,m),                                                bond              6.8-7.5 (10H,m), 5.85 (1H,t),                                                 5.22 (2H,s), 2.7 (2H,m), 2.2 (2H,m).       37 2-Br          Single                                                                            1 N           6.9-8.2 (10H,m), 6.0 (1H,t),                                bond              5.26 (2H,s), 1.8-2.9 (4H,m).               38 2-Cl          Single                                                                            1 N           MP = 60-65° C.                                       bond  (p-CH.sub.3 --C.sub.6 H.sub.4 --SO.sub.3 H)            39 2-Cl          Single                                                                            1 N           MP = 104-110° C.                                     bond  (H.sub.2 SO.sub.4)                                     40 3-CH.sub.3    Single                                                                            1 N           8.05 (1H,m), 7.92 (1H,s),                                   bond              7.86 (1H,s), 6.9-7.5 (7H,m),                                                  5.98 (1H,t), 5.13 (2H,s), 2.7 (2H,m),                                         2.32 (3H,s).                               41 2-CH.sub.3    Single                                                                            1 N           8.1 (1H,m), 7.9 (1H,s),                                     bond              7.8 (1H,s), 6.9-7.5 (7H,m), 5.95                                              (1H,t),                                                                       5.2 (2H,s), 2.75 (2H,m), 2.35 (2H,m),                                         2.2 (3H,s).                                42 4-C(CH.sub.3 ).sub.3                                                                        Single                                                                            1 N           8.14 (1H,m), 7.9 (2H,s + s),                                bond              7.0-7.5 (7H,m), 5.96 (1H, broad t),                                           5.15 (2H,s), 2.75 (2H,m), 2.35                                                (2H,m),                                                                       1.32 (9H,s).                               43 4-CN          Single                                                                            1 N           8.1 (1H,m), 7.98 (2H,s),                                    bond              7.94 (1H,s), 7.0-7.8 (7H,m), 6.0                                              (1H,t),                                                                       5.2 (2H,s), 2.75 (2H,m), 2.4 (2H,m).       44 3-CN          Single                                                                            1 CH          8.0 (1H,m), 7.0-7.6 (9H,m),                                 bond              6.8 (1H,s), 5.82 (1h,t), 5.15 (2H,s),                                         2.7 (2H,m), 2.25 (2H,m).                   45 2-CH.sub.3, 4-C(CH.sub.3).sub.3                                                             S   3 N           7.9-8.2 (2H,m),                                                               7.0-7.4 (7H,m), 5.9 (1H, broad t),                                            4.25 (2H,t), 2.65-3.1 (4H,m),                                                 2.4 (3H,s), 1.8-2.2 (4H,m), 1.3                                               (9H,s).                                    46 4-NO.sub.2    Single                                                                            1 CH          7.9-8.3 (3H,m),                                             bond              6.85-7.7 (8H,m), 5.88 (1H,t),                                                 5.24 (2H,s), 2.75 (2H,m), 2.3 (2H,m).      47 4-CF.sub.3    Single                                                                            1 CH          8.05 (1H,m),                                                bond              6.8-7.7 (10H,m), 5.8 (1H,t), 5.2                                              (2H,s),                                                                       2.5-2.8 (2H,m) 2.0-2.5 (2H,m).             48 4-OCH.sub.2 CH.sub.3                                                                        Single                                                                            1 CH          8.05 (1H,m),                                                bond              6.7-7.5 (10H,m), 5.72 (1H,t),                                                 5.05 (2H,s), 3.94 (2H,q), 2.65                                                (2H,m),                                                                       2.15 (2H,m), 1.34 (3H,t).                  49 2-I           Single                                                                            1 CH          15.5 (1H, broad s),                                         bond  (HCl)       9.2 (1H,s), 7.7-8.2 (2H,m),                                                   6.8-7.5 (8H,m), 6.2 (1H, broad t),                                            5.2 (2H,s), 2.2-2.9 (4H,m).                a  4-CO.sub.2 CH.sub.3                                                                         Single                                                                            1 N           7.85-8.3 (3H,m),                                            bond              7.1-7.5 (7H,m), 6.0 (1H,t), 5.3                                               (2H,s),                                                                       3.9 (3H,s), 2.75 (2H,m), 1.9-2.5                                              (2H,m).                                    a  2-Cl, 6-F     Single                                                                            1 N           MP = 153-158° C.                                     bond  (HCl)                                                  50 4-CO.sub.2 CH.sub.3                                                                         Single                                                                            1 N           7.85-8.3 (3H,m),                                            bond              7.1-7.5 (7H,m), 6.0 (1H,t), 5.3                                               (2H,s),                                                                       3.9 (3H,s), 2.75 (2H,m), 1.9-2.5                                              (2H,m).                                    51 2-Cl,6-F      Single                                                                            1 N           MP = 153-158° C.                                     bond  (HCl)                                                  52 2-I           Single                                                                            1 CH          8.05 (1H,m), 6.8-7.9 (10H,m),                               bond              5.9 (1H,t), 5.22 (2H,s), 2.7 (2H,m),                                          2.25 (2H,m).                               53 4-Cl, 3-NO.sub.2                                                                            Single                                                                            1 CH          8.0 (1H,m), 6.8-7.7 (9H,m), 5.84                                              (1H,t),                                                     bond              5.16 (2H,s), 2.75 (2H,m), 2.3 (2H,m).      54 3-OCH.sub.3   Single                                                                            1 CH          8.1 (1H,m), 6.7-7.5 (10H,m),                                bond              5.82 (1H,t), 5.12 (2H,s), 3.75                                                (3H,s),                                                                       2.7 (2H,m), 2.25 (2H,m),                   55 2-CN          Single                                                                            1 CH          8.05 (1H,m), 6.8-7.7 (10H,m),                               bond              5.88 (1H,t), 5.32 (2H,s), 2.7 (2H,m),                                         2.25 (2H,m).                               56 2-Cl, 6-F     Single                                                                            1 N           8.05 (1H,m), 7.88 (2H, broad s),                            bond              6.8-7.4 (6H,m), 5.9 (1H,t),                                                   5.32 (2H,s), 2.75 (2H,m), 2.35                                                (2H,m).                                    57 [2,3]-CH═CH--CH═CH--                                                                Single                                                                            1 N           7.8-8.2 (3H,m), 6.9-7.6 (10H,m),                            bond              5.88 (1H,t), 5.58 (2H,s), 2.56                                                (2H,m),                                                                       1.8-2.5 (2H,m).                            58 2-CH.sub.3    Single                                                                            1 N           MP = 60-65° C.                                       bond  (HNO.sub.3)                                            59 4-CH.sub.3    Single                                                                            1 N           8.1 (1H,m), 7.9 (1H,s), 7.85 (1H,s),                        bond              6.9-7.5 (7H,m), 5.95 (1H,t),                                                  5.14 (2H,s), 2.75 (2H,m), 2.4 (2H,m),                                         2.32 (3H,s).                               60 4-OCH.sub.3   Single                                                                            1 N           8.1 (1H,m), 7.9 (1H,s), 7.85 (1H,s),                        bond              6.9-7.4 (7H,m), 5.9(1H,t), 5.06                                               (2H,s),                                                                       3.74 (3H,s), 2.7 (2H,m), 2.35 (2Hmn).      61 4-Br          0   2 CH          8.0 (1H,m), 6.6-7.8 (10H,m), 5.78                                             (1H,t),                                                                       4.4 (2H,m), 4.1 (2H,m), 2.7 (2H,m),                                           2.25 (2H,m).                               62 2-CH.sub.3, 4-C(CH.sub.3).sub.3                                                             SO.sub.2                                                                          3 CH          7.9 (3H,m), 7.1-7.5 (6H,m),                                                   5.78(1H, broad t), 4.2(2H,t),                                                 2.6-3.4 (6H,m), 2.32 (3H,s), 2.25                                             (2H,m),                                                                       1.32 (9H,s).                               63 2-Cl, 4-Cl    Single                                                                            1 CH          8.0 (1H,m), 6.8-7.6 (9H,m), 5.82                                              (1H,t),                                                     bond              5.24 (2H,s), 2.7 (2H,m), 2.2 (2H,m).       64 2-Cl, 6-Cl    Single                                                                            1 CH          8.1 (1H,m), 6.76-7.5 (9H,m), 5.8                                              (1H,t),                                                     bond              5.48 (2H,s), 2.7 (2H,m), 2.22 (2H,m).      65 4-C.sub.6 H.sub.5                                                                           Single                                                                            1 N           8.1 (1H,m), 7.9 (2H,s + s),                                 bond              7.0-7.6 (12H,m), 5.95 (1H,t), 5.18                                            (2H,s),                                                                       2.65 (2H,m), 1.9-2.5 (2H,m).               66 3-OC.sub.6 H.sub.5                                                                          Single                                                                            1 CH          8.05 (1H,m), 6.7-7.5 (15H,m),                               bond              5.8 (1H,t), 5.1 (2H,s), 2.55-2.8                                              (2H,m),                                                                       1.9-2.3 (2H,m).                            67 4-OC.sub.6 H.sub.5                                                                          Single                                                                            1 N           8.1 (1H,m), 7.9 (2H,s + s),                                 bond              6.8-7.5 (12H,m), 5.92 (1H,t),                                                 5.1 (2H,s), 2,75 (2H,m), 1.9-2.5                                              (2H,m).                                    68 4-CF.sub.3    Single                                                                            1 CH          15.0 (1H, broad s), 9.5(1H,s),                              bond  (HCl)       8.0 (1H,m), 6.94-7.8 (9H,m),                                                  6.2 (1H, broad t), 5.2 (2H,s),                                                2.2-2.9 (4H,m).                            69 3-Cl, 4-Cl    Single                                                                            1 N           8.1 (1H,m), 7.98 (2H,s + s),                                bond              6.9-7.5 (6H,m), 5.98 (1H,t), 5.1                                              (2H,s),                                                                       2.7 (2H,m), 2.3 (2H,m).                    70 4-Cl          Single                                                                            2 N           8.0 (1H,m), 7.9 (1H,s), 7.85 (1H,s),                        bond              6.9-7.4 (7H,m), 5.8 (1H,t), 4.35                                              (2H,t),                                                                       2.9 (2H,t), 2.7 (2H,m), 2.0-2.5                                               (2H,m).                                    71 4-F           Single                                                                            2 N           8.1 (1H,m), 7.9 (1H,s), 7.85 (1H,s),                        bond              6.8-7.3 (7H,m), 5.9 (1H,t), 4.35                                              (2H,t),                                                                       2.85 (2H,t), 2.65 (2H,m),                                                     2.0-2.5-(2H,m).                            72 2-F           Single                                                                            2 N           8.1 (1H,m), 7.95 (1H,s), 7.9 (1H,s),                        bond              6.9-7.4 (7H,m), 6.0 (1H,5), 4.4                                               (1H,t),                                                                       3.0 (2H,t), 2.6 (2H,m), 1.9-2.5                                               (2H,m).                                    73 2-F           Single                                                                            1 CH          8.0 (1H,m), 6.8-7.5 (10H,m), 5.7                                              (1H,m),                                                     bond              4.3 (2H,t), 3.4 (2H,t), 2.8 (2H,m),                                           2.5 (2H,m).                                74 4-F           Single                                                                            2 CH          8.0 (2H,m), 6.7-7.5 (10H,m), 5.7                            bond              (1H,t), 4.3 (2H,t), 2.8-3.2 (2H,m),                                           2.6 (2H,m), 2.3 (2H,m).                    75 4-F           Single                                                                            4 N           7.8-8.1 (3H,m), 6.8-7.4 (7H,m),                             bond              5.9 (1H,t), 4.1 (2H,t),                                                       2.2-2.8 (6H,m), 1.8-2.2 (2H,m).            76 4-Cl          Single                                                                            3 N           8.1 (1H,m), 7.9 (2H,s + s),                                 bond              5.9 (1H,t), 4.2 (2H,t),                                                       2.3-2.8 (6H,m), 1.8-2.1 (2H,m).            77 4-Cl          Single                                                                            3 CH          8.1 (1H,m), 6.8-7.5 (10H,m),                                bond              5.7 (1H,5), 4.15 (2H,t),                                                      2.2-2.8 (6H,m), 1.8-2.2 (2H,m).            78 4-Br          Single                                                                            2 CH          8.1 (2H,m), 6.8-7.5 (10H,m), 5.75                                             (H,t),                                                      bond              4.35 (2H,t), 2.85 (2H,t), 2.7 (2H,m),                                         2.25 (2H,m).                               79 4-Br          Single                                                                            2 N           8.0 (1H,m), 7.9 (1H,s), 7.8 (1H,s),                         bond              7.8 (1H,s), 6.0-7.4 (7H,m), 5.8                                               (1H,t),                                                                       4.2 (2H,t), 2.8 (2H,t), 2.6 (1H,m),                                           1.9-2.3 (2H,m).                            80 2-Cl          Single                                                                            3 N           8.1 (1H,m), 7.95 (1H,s), 7.9 (1H,s),                        bond              7.9 (1H,s), 6.9-7.4 (7H,m), 5.9                                               (1H,t),                                                                       4.2 (2H,t), 2.2-2.8 (6H,m),                                                   1.8-2.1 (1H,m).                            81 2-Cl          Single                                                                            3 CH          8.0 (1H,m), 6.8-7.4 (10H,m), 5.8                                              (1H,t)                                                      bond              4.2 (2H,t), 2.3-2.8 (6H,m),                                                   1.8-2.1 (2H,m).                            __________________________________________________________________________

EXAMPLE 12 Preparation of Fungicidal and Plant Regulant Compositions

The compounds prepared in Examples 3-10 (Compound Nos. 1-81) were formedinto compositions. This was accomplished by dissolving 0.3 g. of each ofthe compounds in 10 ml. of acetone or other suitable solvent. Each ofthese solutions were treated with 1 to 2 drops of an emulsifying agent,such as Triton X-100, and water was added to form an emulsion. Thedegree of dilution with water was dictated by the desired concentrationof the composition. The greater the quantity of water added the lowerwas the concentration of the composition, reported in milligrams perliter (mg/l).

EXAMPLE 13 Control of Powdery Mildew Fungus (Systemic Root Uptake)

Each of the compounds prepared in accordance with Examples 3-10,Compound Nos. 1-81, were tested to evaluate their effectiveness inpreventing or controlling powdery mildew disease of barley caused by thefungus Erysiphe graminis and powdery mildew disease of cucumber causedby the fungus, Erysiphe cichoracearum. This prevention or controlcapability was tested by utilizing the compounds of the presentinvention to control these diseases by systemic root uptake.

To accomplish this task, pots (4×4×3.5 inches) containing 10 plants ofbarley (Variety "Herta") and cucumber (Variety "Marketmore 70") weregrown to age 6 days and 10 days, respectively. Upon reaching these ages,45 ml. of emulsion compositions formed in accordance with Example 12were added to each pot. That is, 73 pots were treated with emulsioncompositions of the 73 compounds prepared in accordance with Examples 3to 10. The 45 ml. compositions saturated the soil without significantloss through drainage into the saucers below the pots. In addition, anumber of pots containing the same barley and cucumber plants were leftuntreated. These pots were used as controls.

Twenty-four hours after the treatment with the compositions of thepresent invention, both the barley and cucumber plants in all the pots,those treated and those untreated, were inoculated with powdery mildewfungus. This was accomplished by tapping leaves of previously infectedbarley and cucumber plants over the treated and untreated potscontaining the barley and cumber plants, respectively, to distributespores of the fungus over the plants tested.

Six days after inoculation, disease control was evalulated on a 0 to 6rating scale. A 0 rating was assigned when no disease was evidenced anda 6 rating was given for severe disease. Intermediate ratings wereassigned depending on the degree of disease. Percent control wascomputed by comparing the ratings for the treated and untreated plants.

The results of this example, that is, the percent control for each ofthe compounds tested is reported in Table II. The results of the powderymildew disease control of barley is reported under the title "BMS 250".The control of cucumber powdery mildew is similarly reported under thetitle of "CMS 250." It is noted that Table II appears after Example 17.

EXAMPLE 14 Control of Powdery Mildew in Barley by Foliar Application

Eight plants of "Larker" variety barley were planted in a pot. Thenumber of pots were sufficient to accommodate testing in duplicate ortriplicate pots for each of the 48 compounds tabulated in Table I. Thisnumber included a duplicate number of pots which acted as controls aswill be discussed below.

Each of the compounds tabulated in Table 1 were tested by being sprayedonto the plants as compositions, prepared in accordance with Example 12,at a emulsion composition concentration of 1,000 ppm. Compositions ofeach compound were sprayed on two or three pots. An equal number of potswere unsprayed and thus acted as controls. That is for each pot sprayedan unsprayed pot was utilized as a control.

After the leaves of the sprayed pots were dried, they and the unsprayedcontrol pots were placed in a greenhouse maintained at 21° C. All thepots were there inoculated with barley powdery mildew fungus, Erysiphegraminis. This inoculation was accomplished by distributing spores ofthe fungus over the leaves to be tested from plants which had previouslybeen infected with the mildew disease.

Five days after inoculation, the plants were evaluated and assigned adisease rating of 0 to 6 as described in Example 13. Again, percentcontrol was computed by comparing the treatment scores with the scoresof the untreated controls. The results of these tests are summarized inTable II under the title "BMP 1000."

EXAMPLE 15 Control of Rice Blast Disease by Foliar Treatment

Five Bellemont rice plants were grown in a plurality of pots. The numberof pots with planted rice plants were sufficient to test thecompositions of all 73 compounds listed in Table I as well as controlstherefor, the number of controls equal to the number of pots treatedwith each compound.

Three to four weeks after planting, the rice plants were sprayed withcompositions of the compounds of this invention, prepared in accordancewith Example 12. The concentration of each composition was 1,000 mg/l.An equal number of pots, also containing five rice plants per pot,remained unsprayed.

Sprayed and unsprayed pots of the plant were inoculated with spores ofthe rice blast fungus, Pyricularia oryzae. This inoculation wasaccomplished by preparing inoculum containing 20,000 to 30,000 sporesper millilitre. The inoculum so prepared was sprayed on the plants with1 to 2 drops of Tween [trademark]20 surfactant (ethoxylated sorbitanmonolaurate) to insure proper wetting of the inoculum onto the plantleaves.

The plants were incubated in a controlled chamber at a humidity of 99%and a temperature of 21° C. for about 24 hours to allow infection tooccur. The plants, after 24 hours in the control chamber, weretransferred to a greenhouse for six days to permit disease developmentto occur. Disease was manifested by blast lesions on the leaves. Diseasecontrol was calculated by either counting lesions, if infection wasmoderate, or evaluating by the 0 to 6 rating system defined in Example13. Of course, the evaluation system used in rating any of the compoundsof the present invention was also utilized in evaluating its control.The results of this test are also tabulated in Table II under the title"RCB 1000."

EXAMPLE 16 Control of Bean Rust Fungus Eradicant Test

Pots were planted with two pinto bean plants, P. vulgaris each,susceptible to rust disease. When the plants were 7 days old, at theprimary leaf stage of growth, they were all sprayed with a suspensioncontaining 20,000 spores of the bean rust fungus, Uromyces phaseoli, perml. All the pots containing the plants were then incubated in acontrolled environmental chamber, maintained at 99% humidity and 21° C.,for 24 hours to allow infection to occur. The plants were then removedfrom the incubator and allowed to dry. Two days after inoculation theinfected plants were sprayed with compositions formed from the compoundsof this invention, set forth in Example 12, at a dosage of 1,000 mg/l. Anumber of infected plants were not sprayed and acted as controls. All ofthe sprayed and unsprayed plants were then placed in a greenhouse at 21°C. for five days to allow any disease present to be expressed.

All the plants sprayed with the spore suspension were assessed fordisease using the 0 to 6 rating system described in Example 13. Controlof disease was determined by comparing treated plants with the untreatedcontrols. The control of disease, expressed as percent reduction ofdisease, is included in Table III under the title "BRE 1000."

EXAMPLE 17 Control of Nine Fungus Species

Compounds listed in Table I were solubilized in acetone at aconcentration of 500 mg/l for all fungus species. Filter paper discs,each 11 mm. diameter, were dipped in each of the test solutions. Thediscs were allowed to air dry to drive off the acetone solvent. A numberof discs were untreated to provide controls.

The treated and untreated discs were then placed on agar plates and 8fungus species: Alternaria solani (ALT), Botrytis cinerea (BOT),Fusarium oxysporum (FUS) Helminthosporium maydis (HMAY) Phytophthorainfestans (PHY), Sclerotinia sclerotiorum (SCM) and Sclerotium rolfsii(SCO) were added to the center of each test disc in the form of aculture plug with the fungus mat in contact with the treated paper ofthe test disc. Two drops of a ninth fungi species, Cercosporaarachidicola (CER), were added as a spore suspension 20,000 spores/ml)to the chemically treated test disc, rather than a mycelial cultureplug. The plates were incubated at 29° C. in an oven and then the eightfungus species were evaluated by measuring the radius from the center ofthe fungus colony of the treated disc compared to the radius from thecenter of the fungus colony of the untreated discs.

Percent growth inhibition of each of the compounds tested was determinedas a function of the difference between the radii of the treated anduntreated discs for the eight fungus species.

In the case of the Cercospora arachidicola (CER) fungi, scoring was doneon a numerical basis as follows:

100=Complete inhibition of germination and growth.

50=Partial inhibition of growth or, early complete inhibition but latergrowth begins.

0=No inhibition of growth.

                                      TABLE II                                    __________________________________________________________________________    Fungicidal Activity                                                              ALT RMS BOT  BRE CER CMS  FUS HMAY PHY PMP RCB SCM  SCO BMP                Cpd.                                                                             500 250 500  1000                                                                              500 250  500 500  500 1000                                                                              1000                                                                              500  500 1000               No.                                                                              (Ex17)                                                                            (Ex13)                                                                            (Ex17)                                                                             (Ex16)                                                                            (Ex17)                                                                            (Ex13)                                                                             (Ex17)                                                                            (Ex17)                                                                             (Ex17)                                                                            (Ex17)                                                                            (Ex15)                                                                            (Ex17)                                                                             (Ex17)                                                                            (Ex14)             __________________________________________________________________________    1  65  90  50   0   50  20   40  0    85  0   65  25   0   90                 2  55  15  30   0   100 0    50  55   75  0   95  10   0   90                 3  76  15  0    95  100 40   40  80   65  0   95  29   65  100                4  100 40  100  25  100 20   85  100  100 50  --  20   40  --                 5  75  0   75   0   100 20   100 100  80  0   15  5    60  15                 6  35  0   85   75  0   0    50  35   30  80  100 30   10  100                7  50  0   85   80  100 0    50  50   75  50  100 35   0   100                8  35  0   100  0   100 0    65  55   100 0   100 35   0   100                9  95  0   100  0   100 0    75  100  100 0   100 65   75  100                10 100 0   100  50  100 0    100 100  100 90  100 35   0   90                 11 100 0   100  60  100 0    100 100  100 75  100 35   0   100                12 95  35  55   96  100 50   85  100  100 0   --  15   0   --                 13 85  0   50   100 100 50   80  85   100 50  --  0    0   --                 14 75  15  55   100 100 0    80  80   100 50  --  25   0   --                 15 65  15  75   50  100 75   90  85   100 0   50  0    0   85                 16 65  15  50   90  0   50   50  50   75  0   --  15   0   --                 17 55  15  50   0   0   20   0   0    75  50  --  0    0   --                 18 65  15  35   0   0   0    20  50   75  75  50  55   35  100                19 10  15  0    0   0   25   15  20   50  75  65  0    0   100                20 0   35  25   0   0   15   0   0    50  75  65  0    0   100                21 20  0   0    50  0   0    15  0    25  100 15  0    0   40                 22 95  0   20   25  100 90   90  100  100 75  100 0    65  100                23 40  0   0    40  50  15   60  25   55  100 65  45   35  100                24 65  20  50   30  100 35   90  90   100 95  65  0    0   100                25 55  0   0    15  0   15   60  20   75  100 100 25   15  100                26 100 0   25   50  100 15   85  100  100 95  100 0    15  100                27 40  0   0    70  50  35   60  40   55  100 100 35   45  100                28 85  20  100  35  100 0    50  90   100 95  100 40   100 100                29 55  0   0    40  0   0    85  35   75  100 100 25   10  100                30 100 0   100  35  100 15   60  90   100 90  100 10   35  100                31 40  0   10   10  50  0    60  35   80  100 100 0    0   100                32 40  0   0    25  0   15   60  35   45  100 65  25   0   100                33 75  0   25   90  100 35   100 100  100 90  100 10   40  100                34 55  0   0    85  0   15   50  50   80  95  50  25   35  100                35 100 40  100  90  100 0    100 100  100 80  100 45   10  100                36 100 0   50   75  100 15   100 100  100 95  100 0    35  100                37 65  0   35   35  100 15   50  35   55  95  100 0    100 100                38 80  0   0    90  0   60   55  45   100 95  100 0    0   100                39 40  0   0    95  100 0    15  50   100 100 100 35   0   100                40 45  0   75   0   0   20   60  80   75  0   90  0    60  100                41 75  35  90   0   50  40   45  55   80  0   90  0    90  100                42 5   0   25   0   0   0    30  25   70  75  90  0    35  100                43 60  50  100  0   0   20   55  80   90  100 90  0    15  100                44 90  35  90   0   50  40   80  90   100 0   100 40   20  100                45 15  15  0    0   0   0    0   0    0   0   90  40   15  90                 46 90  0   90   0   100 0    90  95   90  0   100 10   55  100                47 95  0   100  0   100 0    90  100  100 0   100 30   65  100                48 70  15  100  0   100 15   90  75   70  0   40  10   70  50                 49 100 0   0    100 100 15   90  85   100 0   100 10   45  100                50 45  0   10   0   0   15   50  25   40  0   0   30   0   50                 51 70  65  70   15  0   15   80  25   60  35  100 0    20  100                52 95  33  100  0   100 35   90  100  100 0   80  20   45  100                53 100 15  100  0   100 15   100 100  75  0   100 0    25  100                54 70  0   100  0   100 0    80  100  25  0   85  0    25  100                55 50  0   50   0   100 15   50  85   25  0   35  0    0   85                 56 80  35  100  0   100 15   50  10   50  0   100 0    25  100                57 50  15  60   0   0   0    10  10   25  0   35  0    0   85                 58 50  0   10   0   0   15   35  10   25  0   40  0    25  100                59 50  35  0    0   0   15   50  55   25  0   35  45   50  100                60 50  0   25   0   0   15   40  45   25  0   85  25   0   65                 61 60  0   75   0   50  35   75  100  25  0   65  0    20  35                 62 25  0   50   0   0   15   0   55   0   0   65  0    0   100                63 100 35  100  0   100 35   85  75   100 0   90  0    45  100                64 100 15  100  0   100 0    85  45   100 0   15  0    50  100                65 60  35  75   0   0   15   35  35   60  0   0   0    0   --                 66 80  35  100  0   100 15   75  65   100 0   0   35   60  --                 67 60  15  9    0   0   15   40  65   65  0   0   10   40  90                 68 85  0   30   0   100 0    85  100  100 0   100 25   10  100                69 75  50  80   70  0   15   60  10   100 50  100 10   30  100                70 75  15  15   0   100 0    5   100  55  100 0   65   0   90                 71 65  15  70   0   50  0    0   100  25  90  0   90   25  --                 72 55  0   95   0   50  0    5   100  15  100 0   90   100 --                 73 15  35  75   0   100 20   0   75   15  0   0   100  40  --                 74 100 0   40   0   100 15   55  100  100 0   0   20   100 0                  75 0   0   10   0   0   0    0   0    0   50  85  0    40  100                76 10  0   0    0   0   0    0   0    0   0   90  0    0   90                 77 60  --  0    0   100 --   65  100  75  --  --  40   40  --                 78 100 0   40   100 100 0    100 100  100 35  100 0    5   100                79 55  0   0    100 100 35   0   100  80  100 75  0    0   100                80 20  0   35   0   0   0    0   50   35  0   90  0    0   90                 81 60  0   75   0   0   100  90  100  80  75  100 70   0   90                 __________________________________________________________________________

Example 18

Growth Regulation of Soybean, Cotton, Bean and Barley Plants

Aqueous compositions of Compound Nos. 1-22, 24-37, 39-42, 44, 52, 61, 65and 70-72 were prepared in accordance with the procedure set forth inExample 12. In particular, these compositions were prepared inconcentrations of 1,000 mg/l and 3,000 mg/l from 450 mg. of the compounddissolved or dispersed in 10 ml. distilled water or an organic solvent,usually acetone, to which 20 mg. of an emulsifying agent, usuallyethoxylated sorbitan monolaurate (Tween [trademark of ICI, America] 20),was added. The solution or dispersion was diluted to 150 ml. withdistilled water, producing a 3,000 mg/l aqueous composition. Byappropriate further dilution with distilled water, a 1,000 mg/l aqueouscomposition was prepared.

The compositions, prepared in accordance with the above procedure, wereatomized with a DeVilbiss [trademark] No. 152 sprayer onto the foliageof soybean plants (Glycine max (L.) Merr. cv. Williams, 2 weeks old),cotton plants (Gossypium hirsutum L. cv. Stoneville 213, 3 to 4 weeksold), bean plants (Phaseolus vulgaris L. cv. Pinto III, 2 weeks old) andbarley plants (Hordeum vulgare L. cv. Herta, 1 week old). Sprayingcontinued until the foliage was wetted to the drip point. After 1 to 3weeks, depending on the plant species, the plants were evaluated forretardation of vegetative growth, ##EQU1## The results of this test aresummarized in Table III.

                  TABLE III                                                       ______________________________________                                        Percent Growth Retardation                                                    Cpd. Bean        Barley    Cotton    Soybean                                  No.  (1000 ppm)  (3000 ppm)                                                                              (3000 ppm,)                                                                             (3000 ppm)                               ______________________________________                                        1    0           0         50        90                                       2    0           0         20        0                                        3    0           0         50        50                                       4    40          0         75        0                                        5    0           0         30        0                                        6    50          0         100       50                                       7    0           0         90        90                                       8    0           0         95        30                                       9    0           0         30        0                                        10   0           0         100       20                                       11   0           0         100       0                                        12   80          0         NT        0                                        13   90          0         NT        0                                        14   50          0         NT        0                                        15   50          0         NT        75                                       16   50          0         NT        0                                        17   80          0         NT        100                                      18   30          0         NT        0                                        19   90          0         NT        0                                        20   20          0         NT        0                                        21   95          0         NT        100                                      22   20          0         NT        0                                        24   20          0         NT        0                                        25   20          0         NT        0                                        26   20          0         NT        0                                        27   15          0         NT        0                                        28   30          0         NT        0                                        29   90          0         NT        0                                        30   50          0         NT        0                                        31   30          50        NT        0                                        32   90          30        NT        0                                        33   50          0         NT        0                                        34   20          0         NT        0                                        35   30          0         NT        0                                        36   20          0         NT        0                                        37   15          40        NT        0                                        39   20          30        NT        0                                        40   20          0         NT        0                                        41   20          0         NT        0                                        42   90          0         NT        0                                        44   20          0         NT        0                                        52   0           0         NT        20                                       61   0           0         NT        20                                       65   0           0         NT        75                                       70   90          0         NT        0                                        71   50          0         NT        100                                      72   90          0         NT        100                                      ______________________________________                                         NT = Not Tested                                                          

The above embodiments and examples are given to illustrate the scope andspirit of the instant invention. These embodiments and examples willmake apparent, to those skilled in the art, other embodiments andexamples. These other embodiments and examples are within thecontemplation of the present invention. Therefore, this invention shouldbe limited only by the appended claims.

What is claimed is:
 1. A compound having the structural formula (I)##STR8## in which: R is a substituent or a group of substituentsrepresenting halogen, low alkyl of 1 to 6 carbon atoms, phenyl, phenoxy,naphthyl, nitro, cyano, low alkoxy, alkoxycarbonyl, or trifluoromethyl;Xis single bond, oxygen, sulfur or sulfonyl: m is an integer from 1 to 4.2. A compound according to claim 1 whereinR is a substituent or a groupof substituents representing halogen, nitro, cyano, low alkoxy ortrifluoromethyl: X is a single bond: m is an integer from 1 to
 4. 3. Aprocess for controlling phytopathogenic fungic comprising applying afungicidally effective amount of the compound of claim 1 to the locusunder attack by said fungi.
 4. A process for controlling phytopathogenicfungi comprising applying the compound of claim 1, at a concentration of10 ppm to 500 ppm, to the soil in which said plants to be protected fromphytopathogenic fungi are grown.
 5. A process for controllingphytopathogenic fungi in a plurality of plants growing in soilcomprising applying the compound of claim 1 as a coating to seeds ofplants to be protected from said phytopathogenic fungi at a coatingconcentration of 5 to 75 grams of the compound of claim 1 per 100 kg. ofsaid seed.
 6. A process for regulating plant growth comprising applyinga plant growth regulant effective amount of the compound of claim 1 tothe plant whose growth is to be regulated.
 7. A fungicidal compositioncomprising a fungicidally effective amount of the compound of claim 1and a carrier therefor.
 8. A plant growth regulant compositioncomprising a plant growth regulant effective amount of the compound ofclaim 1 and a carrier therefor.